JP3848262B2 - Oligofluorenylene compound and organic light-emitting device - Google Patents
Oligofluorenylene compound and organic light-emitting device Download PDFInfo
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- JP3848262B2 JP3848262B2 JP2003006796A JP2003006796A JP3848262B2 JP 3848262 B2 JP3848262 B2 JP 3848262B2 JP 2003006796 A JP2003006796 A JP 2003006796A JP 2003006796 A JP2003006796 A JP 2003006796A JP 3848262 B2 JP3848262 B2 JP 3848262B2
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- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
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- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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Description
【０００１】
【発明の属する技術分野】
本発明は、有機発光素子に関し、詳しくは有機化合物からなる薄膜に電界を印加することにより光を放出する素子に関する。
【０００２】
【従来の技術】
有機発光素子は、陽極と陰極間に蛍光性有機化合物を含む薄膜を挟持させて、各電極から電子およびホール（正孔）を注入することにより、蛍光性化合物の励起子を生成させ、この励起子が基底状態にもどる際に放射される光を利用する素子である。
【０００３】
１９８７年コダック社の研究（非特許文献１）では、陽極にＩＴＯ、陰極にマグネシウム銀の合金をそれぞれ用い、電子輸送材料および発光材料としてアルミニウムキノリノール錯体を用いホール輸送材料にトリフェニルアミン誘導体を用いた機能分離型２層構成の素子で、１０Ｖ程度の印加電圧において１０００ｃｄ／ｍ2程度の発光が報告されている。関連の特許としては，特許文献１〜３等が挙げられる。
【０００４】
また、蛍光性有機化合物の種類を変えることにより、紫外から赤外までの発光が可能であり、最近では様々な化合物の研究が活発に行われている。例えば、特許文献４〜１１等に記載されている。
【０００５】
さらに、上記のような低分子材料を用いた有機発光素子の他にも、共役系高分子を用いた有機発光素子が、ケンブリッジ大学のグループ（非特許文献２）により報告されている。この報告ではポリフェニレンビニレン（ＰＰＶ）を塗工系で成膜することにより、単層で発光を確認している。共役系高分子を用いた有機発光素子の関連特許としては、特許文献１２〜１６等が挙げられる。
【０００６】
このように有機発光素子における最近の進歩は著しく、その特徴は低印加電圧で高輝度、発光波長の多様性、高速応答性、薄型、軽量の発光デバイス化が可能であることから、広汎な用途への可能性を示唆している。
【０００７】
しかしながら、長時間の使用による経時変化や酸素を含む雰囲気気体や湿気などによる劣化等の耐久性の面で未だ多くの問題がある。さらにフルカラーディスプレイ等への応用を考えた場合、現状では更なる高輝度の光出力あるいは高変換効率、高色純度の青、緑、赤色発光が必要である。例えば、特許文献１７には高発光効率材料として、ジアミン化合物が開示されているが、高色純度（色度座標：ｘ，ｙ＝０．１４−０．１５，０．０９−０．１２）の青色発光は得られていない。
【０００８】
【特許文献１】
米国特許第４，５３９，５０７号明細書
【特許文献２】
米国特許第４，７２０，４３２号明細書
【特許文献３】
米国特許第４，８８５，２１１号明細書
【特許文献４】
米国特許第５，１５１，６２９号明細書
【特許文献５】
米国特許第５，４０９，７８３号明細書
【特許文献６】
米国特許第５，３８２，４７７号明細書
【特許文献７】
特開平２−２４７２７８号公報
【特許文献８】
特開平３−２５５１９０号公報
【特許文献９】
特開平５−２０２３５６号公報
【特許文献１０】
特開平９−２０２８７８号公報
【特許文献１１】
特開平９−２２７５７６号公報
【特許文献１２】
米国特許第５，２４７，１９０号明細書
【特許文献１３】
米国特許第５，５１４，８７８号明細書
【特許文献１４】
米国特許第５，６７２，６７８号明細書
【特許文献１５】
特開平４−１４５１９２号公報
【特許文献１６】
特開平５−２４７４６０号公報
【特許文献１７】
特開２００１−５２８６８号公報
【非特許文献１】
Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１，９１３（１９８７）
【非特許文献２】
Ｎａｔｕｒｅ，３４７，５３９（１９９０）
【０００９】
【発明が解決しようとする課題】
本発明は、このような従来技術の問題点を解決するためになされたものであり、極めて純度のよい発光色相を呈し、高効率で高輝度、高寿命の光出力を有する有機発光素子を得られるオリゴフルオレニレン化合物を提供することにある。さらには製造が容易でかつ比較的安価に作成可能な有機発光素子をを得られるオリゴフルオレニレン化合物を提供する事にある。
【００１０】
【課題を解決するための手段】
本発明者等は、上述の課題を解決するために鋭意検討した結果、本発明を完成するに至った。すなわち本発明のオリゴフルオレニレン化合物は、下記式のいずれかで示されることを特徴とし、下記一般式［１］で示される化合物の一種である。
【００１１】
【化２】
（Ｘ1〜Ｘ4は、置換あるいは未置換のアルキル基、アラルキル基、アリール基及び複素環基、置換あるいは未置換のアリーレン基あるいは二価の複素環基からなる連結基を有する置換あるいは未置換のアルケニル基、アルキニル基、アミノ基、アルコキシ基及びスルフィド基、置換あるいは未置換のアリーレン基あるいは二価の複素環基からなる連結基を有する置換のシリル基及びカルボニル基からなる群より選ばれた基であり、同じであっても異なっていてもよい。また、Ｘ1とＸ2、Ｘ3とＸ4は互いに結合し環を形成していてもよい。
【００１３】
Ｒ1〜Ｒ2は、水素原子、置換あるいは未置換のアルキル基、アラルキル基及びアリール基からなる群より選ばれた基であり、Ｒ1とＲ2は同じであっても異なっていてもよく、また異なるフルオレニレン環上のＲ1同士、Ｒ2同士も同じであっても異なっていてもよい。
【００１４】
ｎは１〜２０の整数である。）
【００１５】
【発明の実施の形態】
以下、本発明に関して詳細に説明する。尚、以下、一般式［１］で示されるオリゴフルオレニレン化合物について説明するが、例示化合物４０ａ，７１ｂが本発明のオリゴフルオレニレン化合物である。
【００１６】
まず、本発明のオリゴフルオレニレン化合物について説明する。
【００１７】
本発明のオリゴフルオレニレン化合物は、上記一般式［１］で示される。
【００１８】
ここで、本発明のオリゴフルオレニレン化合物は、上記一般式［１］におけるｎが１〜４の整数であること、即ち、トリフルオレニレン化合物、テトラフルオレニレン化合物、ペンタフルオレニレン化合物、またはヘキサフルオレニレン化合物であることが好ましい。
【００１９】
また、各窒素上の置換基のいずれか一方が、下記一般式［２］で示される少なくともパラあるいはオルト位に置換基を有するフェニル基であることが好ましい。
【００２０】
【化３】
（Ｒ5〜Ｒ9は、水素、ハロゲン基、シアノ基、ニトロ基、置換あるいは未置換のアルキル基、アラルキル基、アリール基、複素環基、アルケニル基、アルキニル基、アミノ基、アルコキシ基及びスルフィド基、置換のシリル基及びカルボニル基からなる群より選ばれた基であり、同じであっても異なっていてもよい。）
【００２２】
また、各窒素上の置換基のいずれか一方が、芳香族多環縮環基あるいは複素環基であることが好ましい。
【００２３】
更には、各窒素上の置換基のいずれか一方が、上記一般式［２］で示される少なくともパラあるいはオルト位に置換基を有するフェニル基であり、他の一方が芳香族多環縮環基あるいは複素環基であることが好ましい。
【００２４】
上記一般式［１］［２］における置換基の具体例を以下に示す。
【００２５】
置換あるいは未置換のアルキル基としては、鎖状、環状のいずれでも良く、メチル基、エチル基、ｎ−プロピル基、ｎ−ブチル基、ｎ−ヘキシル基、ｎ−デシル基、ｉｓｏ−プロピル基、ｉｓｏ−ブチル基、ｔｅｒｔ−ブチル基、ｔｅｒｔ−オクチル基、トリフルオロメチル基、シクロヘキシル基、シクロヘキシルメチル基等が挙げられるが、もちろんこれらに限定されるものではない。
【００２６】
置換あるいは未置換のアラルキル基としては、ベンジル基、フェネチル基等が挙げられるが、もちろんこれらに限定されるものではない。
【００２７】
置換あるいは未置換のアリール基としては、フェニル基、４−メチルフェニル基、４−メトキシフェニル基、４−エチルフェニル基、４−フルオロフェニル基、３，５−ジメチルフェニル基、ジトリルアミノフェニル基、ビフェニル基、ターフェニル基、ナフチル基、アントラセニル基、フェナンスレリル基、ピレニル基、テトラセニル基、ペンタセニル基、フルオレニル基、トリフェニレニル基、ペリレニル基等が挙げられるが、もちろんこれらに限定されるものではない。
【００２８】
置換あるいは未置換の複素環基としては、ピロリル基、ピリジル基、ビピリジル基、メチルピリジル基、ターピロリル基、チエニル基、ターチエニル基、プロピルチエニル基、フリル基、キノリル基、カルバゾリル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基等が挙げられるが、もちろんこれらに限定されるものではない。
【００２９】
置換あるいは未置換のアリーレン基としては、フェニレン基、ビフェニレン基、２，３，５，６−テトラフルオロフェニレン基、２，５−ジメチルフェニレン基、ナフチレン基、アントラセニレン基、フェナンスレニレン基、テトラセニレン基、ペンタセニレン基、ペリレニレン基等が挙げられるが、もちろんこれらに限定されるものではない。
【００３０】
置換あるいは未置換の二価の複素環基としては、フラニレン基、ピロリレン基、ピリジニレン基、ターピリジニレン基、チオフェニレン基、ターチオフェニレン基、オキサゾリレン基、チアゾリレン基、カルバゾリレン等が挙げられるが、もちろんこれらに限定されるものではない。
【００３１】
置換あるいは無置換のアルケニル基としては、ビニル基、アリル基（２−プロペニル基）、１−プロペニル基、ｉｓｏ−プロペニル基、２−ブテニル基等が挙げられるが、もちろんこれらに限定されるものではない。
【００３２】
置換あるいは無置換のアルキニル基としては、アセチレニル基、フェニルアセチレニル基、１−プロピニル基等が挙げられるが、もちろんこれらに限定されるものではない。
【００３３】
置換または未置換のアミノ基としては、アミノ基、メチルアミノ基、エチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、メチルエチルアミノ基、ベンジルアミノ基、メチルベンジルアミノ基、ジベンジルアミノ基、アニリノ基、ジフェニルアミノ基、フェニルトリルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基等が挙げられるが、もちろんこれらに限定されるものではない。
【００３４】
置換あるいは未置換のアルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基、２−エチル−オクチルオキシ基、フェノキシ基、４−ブチルフェノキシ基、ベンジルオキシ基等が挙げられるが、もちろんこれらに限定されるものではない。
【００３５】
置換あるいは未置換のスルフィド基としては、メチルスルフィド基、エチルスルフィド基、フェニルスルフィド基、４−メチルフェニルスルフィド基等が挙げられるが、もちろんこれらに限定されるものではない。
【００３６】
置換のカルボニル基としては、アセチル基、プロピオニル基、イソブチリル基、メタクリロイル基、ベンゾイル基、ナフトイル基、アントライル基、トルオイル基等が挙げられるが、もちろんこれらに限定されるものではない。
【００３７】
上記置換基が有しても良い置換基としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｔｅｒ−ブチル基、オクチル基、ベンジル基、フェネチル基等のアルキル基、アラルキル基、メトキシ基、エトキシ基、プロポキシ基、２−エチル−オクチルオキシ基、フェノキシ基、４−ブチルフェノキシ基、ベンジルオキシ基等のアルコキシ基、フェニル基、４−メチルフェニル基、４−エチルフェニル基、３−クロロフェニル基、３，５−ジメチルフェニル基、トリフェニルアミノ基、ビフェニル基、ターフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基等のアリール基、ピリジル基、ビピリジル基、メチルピリジル基、チエニル基、ターチエニル基、プロピルチエニル基、フリル基、キノリル基、カルバゾリル基、Ｎ−エチルカルバゾリル基等の複素環基、ハロゲン基、シアノ基、ニトロ基が挙げられるが、もちろんこれらに限定されるものではない。
【００３８】
次に一般式［１］で示されるフルオレニレン化合物についてその代表例を挙げる。ただし、これらの化合物に限定されるものではない。
【００３９】
【化４】
【化５】
【化６】
【化７】
【化８】
【化９】
【化１０】
【化１１】
【化１２】
本発明の一般式［１］で示される化合物は、有機発光素子の有機化合物を含む層、特に、発光層、電子輸送層あるいはホール輸送層として有用であり、また真空蒸着法や溶液塗布法などによって形成した層は結晶化などが起こりにくく経時安定性に優れている。
【００４９】
一般式［１］で示される化合物は、剛直な構造を有するフルオレニレンを分子主鎖に導入することにより、より半値幅の狭い発光スペクトル、すなわちより色純度に優れた発光が得られる。さらにストークスシフトが抑えられることで、フルオレニレン鎖の長さを調節することにより、発光波長の移動を抑えながら吸収を長波長側にシフトさせることも可能で、ドーパント材料として用いる場合、相対的に長波長側に発光スペクトルを有するホスト材料の使用も可能となる。また、アミノ基上の置換基Ｘ1〜Ｘ4を調節することにより、発光色の調節も可能となる。
【００５０】
ＡＭ１／ＣＮＤＯＳ計算により振動子強度の予測をした結果、フルオレニレン鎖の長さを２から本発明における３以上とすることにより、振動子強度の増加が示唆された（−Ｎ（Ｔｏｌ）2基および９，９’−ジメチルフルオレニレン鎖からなるフルオレニレン化合物について計算：ｎ＝２，ｏｓｃｉｌｌａｔｏｒ ｓｔｒｎｇｔｈ：２．１２６５２７／ｎ＝３，ｏｓｃｉｌｌａｔｏｒ ｓｔｒｅｎｇｔｈ：２．９７４５８８／ｎ＝５，ｏｓｃｉｌｌａｔｏｒ ｓｔｒｎｇｔｈ：４．１１８２４４）。計算は、分子の基底状態をＧａｕｓｓｉａｎ９８ソフトを用い半経験的なＡＭ１手法により計算し、分子構造を保持した状態で励起状態エネルギーレベルを、ＣＮＤＯＳ法により配置間相互作用を計算することにより算出することにより実行した。振動子強度が増加し、吸収強度（Ａｂｓ）が増加することにより長波長側に発光スペクトルを有するホスト材料とのエネルギー移動もよりスムーズなものとなる。
【００５１】
一般式［１］で示される化合物は、発光層においてドーパント材料、ホスト材料双方の目的で使用でき、高色純度、高発光効率、高寿命素子を得ることができ、特にドーパント材料として使用し、それとエネルギー移動を起こしやすい適切なホスト材料とのコンビネーションにより、高色純度な発光を保持しかつより効率の高い素子を得ることができる。
【００５２】
一般式［１］で示される化合物を発光層においてドーパント材料として用いる場合、ホスト材料に対するドーパント濃度は、好ましくは０．０１％〜５０％、より好ましくは１〜１０％である。また、好ましいホスト材料としては、例えば下記に示される化合物が挙げられるが、もちろんこれらに限定されるものではない。
【００５３】
【化１３】
【化１４】
【化１５】
次に、本発明の有機発光素子について詳細に説明する。
【００５７】
本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に狭持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層、好ましくは発光層が、一般式［１］で示されるフルオレニレン化合物の少なくとも一種を含有する。
【００５８】
図１〜図６に本発明の有機発光素子の好ましい例を示す。
【００５９】
図１は、本発明の有機発光素子の一例を示す断面図である。図１は、基板１上に、陽極２、発光層３及び陰極４を順次設けた構成のものである。ここで使用する発光素子は、それ自体でホール輸送能、エレクトロン輸送能及び発光性の性能を単一で有している場合や、それぞれの特性を有する化合物を混ぜて使う場合に有用である。
【００６０】
図２は、本発明の有機発光素子における他の例を示す断面図である。図２は、基板１上に、陽極２、ホール輸送層５、電子輸送層６及び陰極４を順次設けた構成のものである。この場合は、発光物質はホール輸送性かあるいは電子輸送性のいずれか、あるいは両方の機能を有している材料をそれぞれの層に用い、発光性の無い単なるホール輸送物質あるいは電子輸送物質と組み合わせて用いる場合に有用である。また、この場合、発光層３は、ホール輸送層５あるいは電子輸送層６のいずれかから成る。
【００６１】
図３は、本発明の有機発光素子における他の例を示す断面図である。図３は、基板１上に、陽極２、ホール輸送層５、発光層３，電子輸送層６及び陰極４を順次設けた構成のものである。これは、キャリヤ輸送と発光の機能を分離したものであり、ホール輸送性、電子輸送性、発光性の各特性を有した化合物と適時組み合わせて用いられ、極めて材料選択の自由度が増すとともに、発光波長を異にする種々の化合物が使用できるため、発光色相の多様化が可能になる。さらに、中央の発光層３に各キャリヤあるいは励起子を有効に閉じこめて、発光効率の向上を図ることも可能になる。
【００６２】
図４は、本発明の有機発光素子における他の例を示す断面図である。図４は、図３に対して、ホール注入層７を陽極２側に挿入した構成であり、陽極２とホール輸送層５の密着性改善あるいはホールの注入性改善に効果があり、低電圧化に効果的である。
【００６３】
図５および図６は、本発明の有機発光素子における他の例を示す断面図である。図５および図６は、図３および図４に対してホールあるいは励起子（エキシトン）を陰極４側に抜けることを阻害する層（ホールブロッキング層８）を、発光層３、電子輸送層６間に挿入した構成である。イオン化ポテンシャルの非常に高い化合物をホールブロッキング層８として用いる事により、発光効率の向上に効果的な構成である。
【００６４】
ただし、図１〜図６はあくまで、ごく基本的な素子構成であり、本発明の化合物を用いた有機発光素子の構成はこれらに限定されるものではない。例えば、電極と有機層界面に絶縁性層を設ける、接着層あるいは干渉層を設ける、ホール輸送層がイオン化ポテンシャルの異なる２層から構成される、など多様な層構成をとることができる。
【００６５】
本発明に用いられる一般式［１］で示される化合物は、図１〜図６のいずれの形態でも使用することができる。
【００６６】
本発明は、特に発光層の構成成分として、一般式［１］で示される化合物を用い、更には必要に応じて例えば前述の例示化合物１１４〜１４０等のホスト材料を用いるものであるが、これまで知られているホール輸送性化合物、発光性化合物あるいは電子輸送性化合物などを必要に応じて一緒に使用することもできる。
【００６７】
以下にこれらの化合物例を挙げる。
【００６８】
【化１６】
【化１７】
【化１８】
【化１９】
【化２０】
【化２１】
本発明の有機発光素子において、一般式［１］で示される化合物を含有する層および他の有機化合物を含有する層は、一般には真空蒸着法あるいは、適当な溶媒に溶解させて塗布法により薄膜を形成する。特に塗布法で成膜する場合は、適当な結着樹脂と組み合わせて膜を形成することもできる。
【００７５】
上記結着樹脂としては、広範囲な結着性樹脂より選択でき、たとえばポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリアリレート樹脂、ポリスチレン樹脂、アクリル樹脂、メタクリル樹脂、ブチラール樹脂、ポリビニルアセタール樹脂、ジアリルフタレート樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、ポリスルホン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。また、これらは単独または共重合体ポリマーとして１種または２種以上混合してもよい。
【００７６】
陽極材料としては、仕事関数がなるべく大きなものがよく、例えば、金、白金、ニッケル、パラジウム、コバルト、セレン、バナジウム等の金属単体あるいはこれらの合金、酸化錫、酸化亜鉛、酸化錫インジウム（ＩＴＯ），酸化亜鉛インジウム等の金属酸化物が使用できる。また、ポリアニリン、ポリピロール、ポリチオフェン、ポリフェニレンスルフィド等の導電性ポリマーも使用できる。これらの電極物質は単独で用いてもよく、複数併用することもできる。
【００７７】
一方、陰極材料としては、仕事関数の小さなものがよく、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウム、アルミニウム、インジウム、銀、鉛、錫、クロム等の金属単体あるいは複数の合金として用いることができる。酸化錫インジウム（ＩＴＯ）等の金属酸化物の利用も可能である。また、陰極は一層構成でもよく、多層構成をとることもできる。
【００７８】
本発明で用いる基板としては、特に限定するものではないが、金属製基板、セラミックス製基板等の不透明性基板、ガラス、石英、プラスチックシート等の透明性基板が用いられる。また、基板にカラーフィルター膜、蛍光色変換フィルター膜、誘電体反射膜などを用いて発色光をコントロールする事も可能である。
【００７９】
なお、作成した素子に対して、酸素や水分等との接触を防止する目的で保護層あるいは封止層を設けることもできる。保護層としては、ダイヤモンド薄膜、金属酸化物、金属窒化物等の無機材料膜、フッ素樹脂、ポリパラキシレン、ポリエチレン、シリコーン樹脂、ポリスチレン樹脂等の高分子膜、さらには、光硬化性樹脂等が挙げられる。また、ガラス、気体不透過性フィルム、金属などをカバーし、適当な封止樹脂により素子自体をパッケージングすることもできる。
【００８０】
【実施例】
以下、実施例により本発明をさらに具体的に説明していくが、本発明はこれらに限定されるものではない。尚、本発明のオリゴフルオレニレン化合物に関する実施例は、実施例１，２，５，７，１６，１７である。
【００８１】
＜実施例１＞［例示化合物Ｎｏ．４０ａの製造方法］
【００８２】
【化２２】
窒素気流下、２，７−ジヨード−９，９−ジメチルフルオレン５ｇ（１１．２ｍｍｏｌ）、９，９−ジメチルフルオレン−２−ボロニックアシド９ｇ（２４．７ｍｍｏｌ）を、脱気したトルエン２００ｍｌ、エタノール１００ｍｌの混合溶媒中に溶解、攪拌し、そこに無水炭酸ナトリウム５１ｇを水２５０ｍｌに溶解させ調整した炭酸ナトリウム水溶液２４５ｍｌを滴下した。３０分攪拌した後、テトラキス（トリフェニルホスフィン）パラジウム１４２ｇ（１．２３ｍｍｏｌ）を加えた。８０℃に加熱したオイルバス上で約３時間、加熱攪拌した。反応溶液を室温に戻した後、水１００ｍｌ、酢酸エチル１００ｍｌを加え、水層と有機層を分離し、さらに水層をトルエン及び酢酸エチルで抽出し、前の有機層とあわせ硫酸ナトリウムで乾燥した。溶媒を留去し、残渣をシリカゲルカラムクロマトグラフィー（トルエン：ヘキサン＝１：２）で精製して、トリス（９，９−ジメチルフルオニレン）４．９ｇを得た。
【００８４】
窒素雰囲気下、トリス（９，９−ジメチルフルオニレン）４．５ｇ（７．７９ｍｍｏｌ）をニトロベンゼン１５０ｍｌに加熱溶解させ、６０℃に加熱したオイルバス上で臭素２．５ｇ（１５．６ｍｍｏｌ）をゆっくり滴下し、さらに約２時間攪拌した。アイスバスに移し反応溶液を冷却し、しばらく攪拌した後、沈殿物をろ過した。沈殿物をトルエンから再結晶し、ろ過、乾燥後、トリス（９，９−ジメチルフルオニレン）のジブロモ体３．４ｇを得た。
【００８５】
窒素雰囲気下、パラジウムビス（ベンジリデンアセトン）１５６ｍｇ（０．２７２ｍｍｏｌ）、トリ−ｔｅｒｔ−ブチルホスフィン３３０ｍｇ（１．６３ｍｍｏｌ）をキシレン２０ｍｌに溶解させ、１５分室温で攪拌した。そこに、キシレン５０ｍｌに溶解させたトリス（９，９−ジメチルフルオニレン）のジブロモ体１ｇ（１．３６ｍｍｏｌ）を滴下し、５０℃に加熱したオイルバス上で３０分攪拌した。さらに、Ｎ−（４−メチルフェニル）−Ｎ−（９−フェナンスリル）アミン１．１５ｇ（４．０８ｍｍｏｌ）を２０ｍｌのキシレンに溶解させ滴下し、続いてｔｅｒｔ−ブトキサイドナトリウム５８８ｍｇ（６．１２ｍｍｏｌ）を加えた。１３０℃に加熱したオイルバス上で約５時間、加熱攪拌した。反応溶液を室温に戻した後、水５０ｍｌを加え、水層と有機層を分離し、さらに水層をトルエン及び酢酸エチルで抽出し、前の有機層とあわせ硫酸マグネシウムで乾燥した。溶媒を留去し、残渣をシリカゲルカラムクロマトグラフィー（トルエン：ヘキサン＝１：２）で精製して、例示化合物Ｎｏ．４０ａを１．２ｇ得た。
【００８６】
＜実施例２＞［例示化合物Ｎｏ．７１ｂの製造方法］
【００８７】
【化２３】
窒素気流下、ビス（２−ヨード−９，９−ジメチルフルオレン）５ｇ（７．８４ｍｍｏｌ）、９，９−ジメチルフルオレン−２−ボロニックアシド６．２６ｇ（１７．２ｍｍｏｌ）を、脱気したトルエン２００ｍｌ、エタノール１００ｍｌの混合溶媒中に溶解、攪拌し、そこに無水炭酸ナトリウム３６ｇを水１８０ｍｌに溶解させ調整した炭酸ナトリウム水溶液１７０ｍｌを滴下した。３０分攪拌した後、テトラキス（トリフェニルホスフィン）パラジウム１４２ｇ（０．８６ｍｍｏｌ）を加えた。８０℃に加熱したオイルバス上で約３時間、加熱攪拌した。反応溶液を室温に戻した後、水１００ｍｌ、酢酸エチル１００ｍｌを加え、水層と有機層を分離し、さらに水層をトルエン及び酢酸エチルで抽出し、前の有機層とあわせ硫酸ナトリウムで乾燥した。溶媒を留去し、残渣をシリカゲルカラムクロマトグラフィー（トルエン：ヘキサン＝１：２）で精製して、テトラキス（９，９−ジメチルフルオニレン）３．９２ｇを得た。
【００８９】
窒素雰囲気下、テトラキス（９，９−ジメチルフルオニレン）３ｇ（３．９０ｍｍｏｌ）をニトロベンゼン１５０ｍｌに加熱溶解させ、６０℃に加熱したオイルバス上で臭素１．４ｇ（７．８０ｍｍｏｌ）をゆっくり滴下し、さらに約２時間攪拌した。アイスバスに移し反応溶液を冷却し、しばらく攪拌した後、沈殿物をろ過した。沈殿物をキシレンから再結晶し、ろ過、乾燥後、テトラキス（９，９−ジメチルフルオニレン）のジブロモ体２ｇを得た。
【００９０】
窒素雰囲気下、パラジウムビス（ベンジリデンアセトン）１２４ｍｇ（０．２１６ｍｍｏｌ）、トリ−ｔｅｒｔ−ブチルホスフィン１３０ｍｇ（０．６４８ｍｍｏｌ）をキシレン２０ｍｌに溶解させ、１５分室温で攪拌した。そこに、キシレン５０ｍｌに溶解させたテトラキス（９，９−ジメチルフルオニレン）のジブロモ体１ｇ（１．０８ｍｍｏｌ）を滴下し、５０℃に加熱したオイルバス上で３０分攪拌した。さらに、Ｎ−（１−アントラセニル）−Ｎ−（フェニル）アミン６９４ｍｇ（２．５９ｍｍｏｌ）を２０ｍｌのキシレンに溶解させ滴下し、続いてｔｅｒｔ−ブトキサイドナトリウム３７４ｍｇ（３．８９ｍｍｏｌ）を加えた。１３０℃に加熱したオイルバス上で約７時間、加熱攪拌した。反応溶液を室温に戻した後、水５０ｍｌを加え、水層と有機層を分離し、さらに水層をトルエン及び酢酸エチルで抽出し、前の有機層とあわせ硫酸マグネシウムで乾燥した。溶媒を留去し、残渣をシリカゲルカラムクロマトグラフィー（トルエン：ヘキサン＝１：２）で精製して、例示化合物Ｎｏ．７１ｂを９００ｍｇ得た。
【００９１】
＜実施例３＞
図３に示す構造の有機発光素子を以下に示す方法で作成した。
【００９２】
基板１としてのガラス基板上に、陽極２としての酸化錫インジウム（ＩＴＯ）をスパッタ法にて１２０ｎｍの膜厚で成膜したものを透明導電性支持基板として用いた。これをアセトン、イソプロピルアルコール（ＩＰＡ）で順次超音波洗浄し、次いでＩＰＡで煮沸洗浄後乾燥した。さらに、ＵＶ／オゾン洗浄したものを透明導電性支持基板として使用した。
【００９３】
正孔輸送材料として下記構造式で示される化合物を用いて、濃度が０．５ｗｔ％となるようにクロロホルム溶液を調整した。
【００９４】
【化２４】
この溶液を上記の陽極２上に滴下し、最初に５００ＲＰＭの回転で１０秒、次に１０００ＲＰＭの回転で１分間スピンコートを行い膜形成した。この後１０分間、８０℃の真空オーブンで乾燥し、薄膜中の溶剤を完全に除去した。形成されたホール輸送層の厚みは５０ｎｍであった。
【００９６】
次に、ホール輸送層５の上に発光層３として前記例示化合物Ｎｏ．２ａを蒸着して２０ｎｍの発光層３を設けた。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【００９７】
更に、電子輸送層６としてアルミニウムキノリノール（Ａｌｑ３）を真空蒸着法にて４０ｎｍの膜厚に形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件であった。
【００９８】
次に、アルミニウム−リチウム合金（リチウム濃度１原子％）からなる蒸着材料を用いて、先ほどの有機層の上に、真空蒸着法により厚さ１０ｎｍの金属層膜を形成し、更に真空蒸着法により厚さ１５０ｎｍのアルミニウム膜を設け、アルミニウム−リチウム合金膜を電子注入電極（陰極４）とする有機発光素子を作成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【００９９】
得られた有機ＥＬ素子は、水分の吸着によって素子劣化が起こらないように、乾燥空気雰囲気中で保護用ガラス板をかぶせ、アクリル樹脂系接着材で封止した。
【０１００】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、６Ｖの印加電圧で、発光輝度１６００ｃｄ／ｍ2、最高輝度９１００ｃｄ／ｍ2、発光効率１．２５ｌｍ／Ｗの発光が観測された。
【０１０１】
＜実施例４〜９＞
例示化合物Ｎｏ．２ａに代えて、表１に示す化合物を用いた他は実施例３と同様に素子を作成し、同様な評価を行った。その結果を表１に示す。
【０１０２】
【表１】
＜実施例１０＞
図３に示す構造の有機発光素子を以下に示す方法で作成した。
【０１０４】
実施例３と同様に、透明導電性支持基板上にホール輸送層５を形成した。
【０１０５】
次に、ホール輸送層５の上に発光層３として前記例示化合物Ｎｏ．６ｂを蒸着して２０ｎｍの発光層３を設けた。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１０６】
更に、バソフェナントロリン（ＢＰｈｅｎ）を真空蒸着法により４０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１０７】
次に、実施例１と同様にして陰極４を形成した後に封止した。
【０１０８】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、６Ｖの印加電圧で、発光輝度２２５０ｃｄ／ｍ2、最高輝度１１７５０ｃｄ／ｍ2、発光効率１．３９ｌｍ／Ｗの発光が観測された。
【０１０９】
＜実施例１１〜１４＞
例示化合物Ｎｏ．６ｂに代えて、表２に示す化合物を用いた他は実施例１０と同様に素子を作成し、同様な評価を行った。その結果を表２に示す。
【０１１０】
【表２】
＜実施例１５＞
発光層３として前記例示化合物Ｎｏ．２３および前記例示化合物Ｎｏ．１２０（重量比４：１００）を共蒸着し２０ｎｍの発光層３を設けた以外は、実施例３と同様にして素子を作成した。
【０１１２】
この様にして得られた素子に、ＩＴＯ電極２を正極、Ａｌ−Ｌｉ電極４を負極にして、４Ｖの印加電圧で、発光輝度１１００ｃｄ／ｍ2、最高輝度２７７００ｃｄ／ｍ2、発光効率２．２５ｌｍ／Ｗの発光が観測された。
【０１１３】
＜実施例１６〜１８＞
例示化合物Ｎｏ．２３に代えて、表３に示す化合物を用いた他は実施例１５と同様に素子を作成し、同様な評価を行った。その結果を表３に示す。
【０１１４】
【表３】
＜実施例１９〜２１＞
例示化合物Ｎｏ．１２０に代えて、表４に示す化合物を用いた他は実施例１５と同様に素子を作成し、同様な評価を行った。その結果を表４に示す。
【０１１６】
【表４】
＜実施例２２＞
発光層３として前記例示化合物Ｎｏ．２３および前記例示化合物Ｎｏ．１２０（重量比４：１００）を共蒸着し２０ｎｍの発光層３を設けた以外は、実施例１０と同様にして素子を作成した。
【０１１８】
この様にして得られた素子に、ＩＴＯ電極２を正極、Ａｌ−Ｌｉ電極４を負極にして、４Ｖの印加電圧で、発光輝度１８９０ｃｄ／ｍ２、最高輝度２９２００ｃｄ／ｍ２、発光効率２．５０ｌｍ／Ｗの発光が観測された。
【０１１９】
＜実施例２３〜２５＞
例示化合物Ｎｏ．２３に代えて、表５に示す化合物を用いた他は実施例１５と同様に素子を作成し、同様な評価を行った。その結果を表５に示す。
【０１２０】
【表５】
＜実施例２６〜２８＞
例示化合物Ｎｏ．１２０に代えて、表６に示す化合物を用いた他は実施例１５と同様に素子を作成し、同様な評価を行った。その結果を表６に示す。
【０１２２】
【表６】
＜実施例２９＞
実施例２６で作成した素子に、窒素雰囲気下で電流密度を７．０ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度４００ｃｄ／ｍ2から１００時間後、３８０ｃｄ／ｍ2と輝度劣化は小さかった。
【０１２４】
＜実施例３０〜３４＞
実施例４，５，１１，１９，２２で作成した素子の発光スペクトルをＭＣＰＤ−７０００で観測し、ＣＩＥ色度座標を測定した。その結果を表７に示す。
【０１２５】
【表７】
＜比較例１＞
発光層３として下記比較化合物を用いた以外は、実施例１０と同様にして素子を作成した。
【０１２７】
【化２５】
この様にして得られた素子に、ＩＴＯ電極２を正極、Ａｌ−Ｌｉ電極４を負極にして、６Ｖの印加電圧で、発光輝度９４０ｃｄ／ｍ2、最高輝度５０５０ｃｄ／ｍ2、発光効率０．６３ｌｍ／Ｗの発光が観測された。
【０１２９】
また、この素子の発光スペクトルをＭＣＰＤ−７０００で観測し、ＣＩＥ色度座標を測定したところ、（ｘ，ｙ）＝（０．１６，０．２９）であった。
【０１３０】
＜比較例２＞
発光層３として上記比較化合物と前記例示化合物１２９（重量比４：１００）を共蒸着し２０ｎｍの発光層３を設けた以外は、実施例１０と同様にして素子を作成した。
【０１３１】
この様にして得られた素子に、ＩＴＯ電極２を正極、Ａｌ−Ｌｉ電極４を負極にして、６Ｖの印加電圧で、発光輝度１０６０ｃｄ／ｍ2、最高輝度９２７０ｃｄ／ｍ2、発光効率０．８２ｌｍ／Ｗの発光が観測された。
【０１３２】
また、この素子の発光スペクトルをＭＣＰＤ−７０００で観測し、ＣＩＥ色度座標を測定したところ、（ｘ，ｙ）＝（０．１６，０．２７）であった。
【０１３３】
【発明の効果】
以上説明のように、一般式［１］で示される化合物を用いた有機発光素子は、極めて純度のよい発光色相を呈し、高効率で高輝度、高寿命の光出力を有する。特に一般式［１］で示される化合物を含有する有機層は、発光層として優れている。
【０１３４】
さらに、素子の作成も真空蒸着あるいはキャステイング法等を用いて作成可能であり、比較的安価で大面積の素子を容易に作成できる。
【図面の簡単な説明】
【図１】本発明における有機発光素子の一例を示す断面図である。
【図２】本発明における有機発光素子の他の例を示す断面図である。
【図３】本発明における有機発光素子の他の例を示す断面図である。
【図４】本発明における有機発光素子の他の例を示す断面図である。
【図５】本発明における有機発光素子の他の例を示す断面図である。
【符号の説明】
１ 基板
２ 陽極
３ 発光層
４ 陰極
５ ホール輸送層
６ 電子輸送層
７ ホール注入層
８ ホール／エキシトンブロッキング層[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an organic light-emitting device, and more particularly to a device that emits light by applying an electric field to a thin film made of an organic compound.
[0002]
[Prior art]
An organic light-emitting element generates an exciton of a fluorescent compound by sandwiching a thin film containing a fluorescent organic compound between an anode and a cathode and injecting electrons and holes from each electrode. It is an element that utilizes light emitted when the child returns to the ground state.
[0003]
In 1987, Kodak Research (Non-patent Document 1) used ITO for the anode and magnesium silver alloy for the cathode, an aluminum quinolinol complex for the electron transport material and the light emitting material, and a triphenylamine derivative for the hole transport material. It has been reported that light emission of about 1000 cd / m 2 at an applied voltage of about 10 V has been reported. Examples of related patents include Patent Documents 1 to 3 and the like.
[0004]
In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared is possible, and recently, various compounds have been actively researched. For example, it describes in patent documents 4-11.
[0005]
Furthermore, in addition to the organic light emitting device using the low molecular material as described above, an organic light emitting device using a conjugated polymer has been reported by a group of Cambridge University (Non-Patent Document 2). In this report, light emission was confirmed in a single layer by forming a film of polyphenylene vinylene (PPV) in a coating system. Patents 12 to 16 and the like can be cited as related patents of organic light emitting devices using conjugated polymers.
[0006]
As described above, recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, low profile, and light-emitting devices with low applied voltage. Suggests the possibility to.
[0007]
However, there are still many problems in terms of durability, such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen or moisture. Further, when considering application to a full-color display or the like, at present, light output with higher luminance or higher conversion efficiency and higher color purity of blue, green, and red light emission is required. For example, Patent Document 17 discloses a diamine compound as a high luminous efficiency material, but high color purity (chromaticity coordinates: x, y = 0.14-0.15, 0.09-0.12). The blue emission of is not obtained.
[0008]
[Patent Document 1]
US Pat. No. 4,539,507 [Patent Document 2]
US Pat. No. 4,720,432 [Patent Document 3]
US Pat. No. 4,885,211 [Patent Document 4]
US Pat. No. 5,151,629 [Patent Document 5]
US Pat. No. 5,409,783 [Patent Document 6]
US Pat. No. 5,382,477 [Patent Document 7]
JP-A-2-247278 [Patent Document 8]
JP-A-3-255190 [Patent Document 9]
JP-A-5-202356 [Patent Document 10]
Japanese Patent Laid-Open No. 9-202878 [Patent Document 11]
JP-A-9-227576 [Patent Document 12]
US Pat. No. 5,247,190 [Patent Document 13]
US Pat. No. 5,514,878 [Patent Document 14]
US Pat. No. 5,672,678 [Patent Document 15]
JP-A-4-145192 [Patent Document 16]
JP-A-5-247460 [Patent Document 17]
JP 2001-52868 A Non-Patent Document 1
Appl. Phys. Lett. 51,913 (1987)
[Non-Patent Document 2]
Nature, 347, 539 (1990)
[0009]
[Problems to be solved by the invention]
The present invention has been made to solve such problems of the prior art, and provides an organic light emitting device that exhibits a light emission hue with extremely high purity, high efficiency, high brightness, and long life light output. It is to provide an oligofluorenylene compound. It is another object of the present invention to provide an oligofluorenylene compound that can be produced easily and can be produced at a relatively low cost.
[0010]
[Means for Solving the Problems]
As a result of intensive investigations to solve the above-mentioned problems, the present inventors have completed the present invention. That is, the oligofluorenylene compound of the present invention is represented by any one of the following formulas and is a kind of a compound represented by the following general formula [1].
[0011]
[Chemical 2]
(X 1 to X 4 are a substituted or unsubstituted alkyl group, aralkyl group, aryl group and heterocyclic group, a substituted or unsubstituted group having a linking group consisting of a substituted or unsubstituted arylene group or a divalent heterocyclic group. Selected from the group consisting of a substituted silyl group and a carbonyl group having a linking group consisting of a substituted or unsubstituted arylene group or a divalent heterocyclic group, an alkenyl group, an alkynyl group, an amino group, an alkoxy group and a sulfide group. The groups may be the same or different, and X 1 and X 2 , X 3 and X 4 may be bonded to each other to form a ring.
[0013]
R 1 and R 2 are groups selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, an aralkyl group and an aryl group, and R 1 and R 2 may be the same or different. In addition, R 1 and R 2 on different fluorenylene rings may be the same or different.
[0014]
n is an integer of 1-20. )
[0015]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail. Hereinafter, the oligofluorenylene compound represented by the general formula [1] will be described, but the exemplified compounds 40a and 71b are the oligofluorenylene compounds of the present invention.
[0016]
First, the oligofluorenylene compound of the present invention will be described.
[0017]
The oligofluorenylene compound of the present invention is represented by the above general formula [1].
[0018]
Here, in the oligofluorenylene compound of the present invention, n in the general formula [1] is an integer of 1 to 4, that is, a trifluorenylene compound, a tetrafluorenylene compound, a pentafluorenylene compound, Or it is preferable that it is a hexafluorenylene compound.
[0019]
Moreover, it is preferable that any one of the substituents on each nitrogen is a phenyl group having a substituent at least in the para or ortho position represented by the following general formula [2].
[0020]
[Chemical 3]
(R 5 to R 9 are hydrogen, halogen group, cyano group, nitro group, substituted or unsubstituted alkyl group, aralkyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, amino group, alkoxy group and sulfide. A group selected from the group consisting of a group, a substituted silyl group and a carbonyl group, which may be the same or different.)
[0022]
Moreover, it is preferable that any one of the substituents on each nitrogen is an aromatic polycyclic fused ring group or a heterocyclic group.
[0023]
Furthermore, one of the substituents on each nitrogen is a phenyl group having a substituent at least in the para or ortho position represented by the general formula [2], and the other is an aromatic polycyclic fused ring group. Or it is preferable that it is a heterocyclic group.
[0024]
Specific examples of the substituents in the general formulas [1] and [2] are shown below.
[0025]
The substituted or unsubstituted alkyl group may be a chain or a ring, and may be a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-hexyl group, an n-decyl group, an iso-propyl group, An iso-butyl group, a tert-butyl group, a tert-octyl group, a trifluoromethyl group, a cyclohexyl group, a cyclohexylmethyl group and the like can be mentioned, but of course not limited thereto.
[0026]
Examples of the substituted or unsubstituted aralkyl group include, but are not limited to, a benzyl group and a phenethyl group.
[0027]
Examples of the substituted or unsubstituted aryl group include phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-ethylphenyl group, 4-fluorophenyl group, 3,5-dimethylphenyl group, and ditolylaminophenyl group. , Biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, triphenylenyl group, perylenyl group, and the like, but are not limited thereto.
[0028]
Substituted or unsubstituted heterocyclic groups include pyrrolyl, pyridyl, bipyridyl, methylpyridyl, terpyrrolyl, thienyl, tertienyl, propylthienyl, furyl, quinolyl, carbazolyl, oxazolyl, oxadiazolyl Group, thiazolyl group, thiadiazolyl group and the like, but of course, it is not limited thereto.
[0029]
Substituted or unsubstituted arylene groups include phenylene, biphenylene, 2,3,5,6-tetrafluorophenylene, 2,5-dimethylphenylene, naphthylene, anthracenylene, phenanthrenylene, tetracenylene Group, pentacenylene group, peryleneylene group and the like, but of course not limited thereto.
[0030]
Examples of the substituted or unsubstituted divalent heterocyclic group include a furanylene group, a pyrrolylene group, a pyridinylene group, a terpyridinylene group, a thiophenylene group, a terthiophenylene group, an oxazolylene group, a thiazolylene group, and a carbazolylene. It is not limited to.
[0031]
Examples of the substituted or unsubstituted alkenyl group include a vinyl group, an allyl group (2-propenyl group), a 1-propenyl group, an iso-propenyl group, a 2-butenyl group, and the like. Absent.
[0032]
Examples of the substituted or unsubstituted alkynyl group include, but are not limited to, an acetylenyl group, a phenylacetylenyl group, and a 1-propynyl group.
[0033]
Examples of the substituted or unsubstituted amino group include amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, methylethylamino group, benzylamino group, methylbenzylamino group, dibenzylamino group, anilino group, A diphenylamino group, a phenyltolylamino group, a ditolylamino group, a dianisolylamino group, etc. are mentioned, but of course, it is not limited to these.
[0034]
Examples of the substituted or unsubstituted alkoxy group include methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, phenoxy group, 4-butylphenoxy group, benzyloxy group and the like. It is not something.
[0035]
Examples of the substituted or unsubstituted sulfide group include, but are not limited to, a methyl sulfide group, an ethyl sulfide group, a phenyl sulfide group, a 4-methylphenyl sulfide group, and the like.
[0036]
Examples of the substituted carbonyl group include, but are not limited to, an acetyl group, a propionyl group, an isobutyryl group, a methacryloyl group, a benzoyl group, a naphthoyl group, an anthryl group, and a toluoyl group.
[0037]
Examples of the substituent that the substituent may have include an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a ter-butyl group, an octyl group, a benzyl group, and a phenethyl group, and an aralkyl group. , Alkoxy group such as methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, phenoxy group, 4-butylphenoxy group, benzyloxy group, phenyl group, 4-methylphenyl group, 4-ethylphenyl group, Aryl group such as 3-chlorophenyl group, 3,5-dimethylphenyl group, triphenylamino group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, pyridyl group, bipyridyl group, methylpyridyl group , Thienyl group, tertienyl group, propylthienyl group, furyl group, quinolyl group, cal Zoriru group, a heterocyclic group such as N- ethyl-carbazolyl group, a halogen group, a cyano group, there may be mentioned a nitro group, but the present invention is of course not limited thereto.
[0038]
Next, typical examples of the fluorenylene compound represented by the general formula [1] will be given. However, it is not limited to these compounds.
[0039]
[Formula 4]
[Chemical formula 5]
[Chemical 6]
[Chemical 7]
[Chemical 8]
[Chemical 9]
[Chemical Formula 10]
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The compound represented by the general formula [1] of the present invention is useful as a layer containing an organic compound of an organic light-emitting device, in particular, as a light-emitting layer, an electron transport layer or a hole transport layer. The layer formed by the method is less susceptible to crystallization and has excellent temporal stability.
[0049]
In the compound represented by the general formula [1], by introducing fluorenylene having a rigid structure into the molecular main chain, an emission spectrum with a narrower half-value width, that is, emission with better color purity can be obtained. Furthermore, by suppressing the Stokes shift, it is possible to shift the absorption to the longer wavelength side while suppressing the shift of the emission wavelength by adjusting the length of the fluorenylene chain. A host material having an emission spectrum on the wavelength side can also be used. In addition, the emission color can be adjusted by adjusting the substituents X 1 to X 4 on the amino group.
[0050]
As a result of the prediction of the oscillator strength by the AM1 / CNDOS calculation, an increase in the oscillator strength was suggested by changing the length of the fluorenylene chain from 2 to 3 or more in the present invention (-N (Tol) 2 group and Calculation for a fluorenylene compound comprising a 9,9′-dimethylfluorenylene chain: n = 2, oscillator strength: 2.126527 / n = 3, oscillator strength: 2.974588 / n = 5, oscillator strength: 4.118244) . The calculation is to calculate the ground state of the molecule by the semi-empirical AM1 method using Gaussian 98 software, and calculate the excited state energy level while maintaining the molecular structure by calculating the configuration interaction by the CNDOS method. Executed by. As the oscillator strength increases and the absorption strength (Abs) increases, energy transfer with the host material having an emission spectrum on the longer wavelength side becomes smoother.
[0051]
The compound represented by the general formula [1] can be used for the purpose of both a dopant material and a host material in the light emitting layer, and can obtain a high color purity, a high light emission efficiency, and a long lifetime device, and particularly used as a dopant material. By combining it with an appropriate host material that easily causes energy transfer, it is possible to obtain a highly efficient device that retains light emission with high color purity.
[0052]
When the compound represented by the general formula [1] is used as a dopant material in the light emitting layer, the dopant concentration with respect to the host material is preferably 0.01% to 50%, more preferably 1 to 10%. Preferred host materials include, for example, compounds shown below, but are not limited to these.
[0053]
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Next, the organic light emitting device of the present invention will be described in detail.
[0057]
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a layer including a pair of electrodes composed of an anode and a cathode and one or more organic compounds sandwiched between the pair of electrodes. At least one of the layers, preferably the light emitting layer, contains at least one fluorenylene compound represented by the general formula [1].
[0058]
1 to 6 show preferred examples of the organic light emitting device of the present invention.
[0059]
FIG. 1 is a cross-sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially provided on a substrate 1. The light-emitting element used here is useful when the device itself has a hole transport ability, an electron transport ability, and a light-emitting performance, or when a compound having each characteristic is used in combination.
[0060]
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an anode 2, a hole transport layer 5, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the light emitting material is either a hole transporting property or an electron transporting property, or a material having both functions is used for each layer, and it is combined with a simple hole transporting material or an electron transporting material having no light emitting property. This is useful when used. In this case, the light emitting layer 3 is composed of either the hole transport layer 5 or the electron transport layer 6.
[0061]
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. This is a function that separates the functions of carrier transport and light emission, and is used in combination with compounds having hole transport properties, electron transport properties, and light emission properties in a timely manner, and the degree of freedom of material selection is greatly increased. Since various compounds having different emission wavelengths can be used, the emission hue can be diversified. Further, it is possible to effectively confine each carrier or exciton in the central light emitting layer 3 to improve the light emission efficiency.
[0062]
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 4 shows a configuration in which a hole injection layer 7 is inserted on the anode 2 side with respect to FIG. 3, and is effective in improving the adhesion between the anode 2 and the hole transport layer 5 or improving the hole injection property. It is effective.
[0063]
5 and 6 are cross-sectional views showing other examples of the organic light-emitting device of the present invention. 5 and 6 show a layer (hole blocking layer 8) that prevents holes or excitons (excitons) from passing to the cathode 4 side as compared with FIGS. 3 and 4 between the light emitting layer 3 and the electron transport layer 6. It is the structure inserted in. By using a compound having a very high ionization potential as the hole blocking layer 8, the structure is effective in improving the light emission efficiency.
[0064]
However, FIG. 1 to FIG. 6 are very basic device configurations, and the configuration of the organic light emitting device using the compound of the present invention is not limited thereto. For example, various layer configurations such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or an interference layer, and the hole transport layer including two layers having different ionization potentials can be employed.
[0065]
The compound represented by the general formula [1] used in the present invention can be used in any form of FIGS.
[0066]
In the present invention, in particular, the compound represented by the general formula [1] is used as a constituent of the light emitting layer, and further, for example, a host material such as the above-described exemplary compounds 114 to 140 is used as necessary. A hole transporting compound, a light emitting compound, an electron transporting compound, etc. known to date can be used together if necessary.
[0067]
Examples of these compounds are given below.
[0068]
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In the organic light-emitting device of the present invention, the layer containing the compound represented by the general formula [1] and the layer containing another organic compound are generally formed into a thin film by a vacuum deposition method or a coating method by dissolving in an appropriate solvent. Form. In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.
[0075]
The binder resin can be selected from a wide range of binder resins such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, diallyl phthalate. Resins, phenol resins, epoxy resins, silicone resins, polysulfone resins, urea resins and the like can be mentioned, but are not limited thereto. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer.
[0076]
As the anode material, one having a work function as large as possible is preferable. For example, simple metals such as gold, platinum, nickel, palladium, cobalt, selenium, vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide (ITO) Metal oxides such as zinc indium oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination.
[0077]
On the other hand, the cathode material preferably has a small work function, and can be used as a single metal or a plurality of alloys such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver, lead, tin, and chromium. it can. A metal oxide such as indium tin oxide (ITO) can also be used. Further, the cathode may have a single layer structure or a multilayer structure.
[0078]
Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.
[0079]
Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of protective layers include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluororesins, polyparaxylene, polyethylene, silicone resins, and polystyrene resins, and photocurable resins. Can be mentioned. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.
[0080]
【Example】
EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. Examples relating to the oligofluorenylene compound of the present invention are Examples 1, 2, 5, 7, 16, and 17.
[0081]
<Example 1> [Exemplary Compound No. 1] Method for producing 40a]
[0082]
Embedded image
Under a nitrogen stream, 2,7-diiodo-9,9-dimethylfluorene 5 g (11.2 mmol) and 9,9-dimethylfluorene-2-boronic acid 9 g (24.7 mmol) were degassed in 200 ml of toluene and ethanol. It melt | dissolved and stirred in 100 ml of mixed solvents, and 245 ml of sodium carbonate aqueous solution which dissolved 51 g of anhydrous sodium carbonate in 250 ml of water was dripped there. After stirring for 30 minutes, 142 g (1.23 mmol) of tetrakis (triphenylphosphine) palladium was added. The mixture was heated and stirred for about 3 hours on an oil bath heated to 80 ° C. After returning the reaction solution to room temperature, 100 ml of water and 100 ml of ethyl acetate were added, the aqueous layer and the organic layer were separated, and the aqueous layer was further extracted with toluene and ethyl acetate, and combined with the previous organic layer and dried over sodium sulfate. . The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene: hexane = 1: 2) to obtain 4.9 g of tris (9,9-dimethylfluorylene).
[0084]
Under a nitrogen atmosphere, 4.5 g (7.79 mmol) of tris (9,9-dimethylfluorene) was dissolved in 150 ml of nitrobenzene by heating, and 2.5 g (15.6 mmol) of bromine was slowly added on an oil bath heated to 60 ° C. The solution was added dropwise and further stirred for about 2 hours. The reaction solution was transferred to an ice bath, cooled, stirred for a while, and then the precipitate was filtered. The precipitate was recrystallized from toluene, filtered and dried to obtain 3.4 g of tribromo (9,9-dimethylfluorylene) dibromo.
[0085]
Under a nitrogen atmosphere, 156 mg (0.272 mmol) of palladium bis (benzylideneacetone) and 330 mg (1.63 mmol) of tri-tert-butylphosphine were dissolved in 20 ml of xylene and stirred at room temperature for 15 minutes. Thereto was added dropwise 1 g (1.36 mmol) of a dibromo tris (9,9-dimethylfluorene) dissolved in 50 ml of xylene, and the mixture was stirred for 30 minutes on an oil bath heated to 50 ° C. Further, 1.15 g (4.08 mmol) of N- (4-methylphenyl) -N- (9-phenanthryl) amine was dissolved in 20 ml of xylene and added dropwise, followed by 588 mg (6.12 mmol) of sodium tert-butoxide. ) Was added. The mixture was heated and stirred for about 5 hours on an oil bath heated to 130 ° C. After returning the reaction solution to room temperature, 50 ml of water was added, the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene and ethyl acetate, combined with the previous organic layer, and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene: hexane = 1: 2). 1.2g of 40a was obtained.
[0086]
<Example 2> [Exemplary Compound No. Manufacturing method of 71b]
[0087]
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Under nitrogen stream, bis (2-iodo-9,9-dimethylfluorene) 5 g (7.84 mmol) and 9,9-dimethylfluorene-2-boronic acid 6.26 g (17.2 mmol) were degassed toluene. Dissolved and stirred in a mixed solvent of 200 ml and 100 ml of ethanol, 170 ml of an aqueous sodium carbonate solution prepared by dissolving 36 g of anhydrous sodium carbonate in 180 ml of water was added dropwise thereto. After stirring for 30 minutes, 142 g (0.86 mmol) of tetrakis (triphenylphosphine) palladium was added. The mixture was heated and stirred for about 3 hours on an oil bath heated to 80 ° C. After returning the reaction solution to room temperature, 100 ml of water and 100 ml of ethyl acetate were added, the aqueous layer and the organic layer were separated, and the aqueous layer was further extracted with toluene and ethyl acetate, and combined with the previous organic layer and dried over sodium sulfate. . The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene: hexane = 1: 2) to obtain 3.92 g of tetrakis (9,9-dimethylfluorene).
[0089]
Under a nitrogen atmosphere, 3 g (3.90 mmol) of tetrakis (9,9-dimethylfluorene) was dissolved in 150 ml of nitrobenzene by heating, and 1.4 g (7.80 mmol) of bromine was slowly added dropwise on an oil bath heated to 60 ° C. The mixture was further stirred for about 2 hours. The reaction solution was transferred to an ice bath, cooled, stirred for a while, and then the precipitate was filtered. The precipitate was recrystallized from xylene, filtered and dried to obtain 2 g of a tetrabromo (9,9-dimethylfluorene) dibromo product.
[0090]
Under a nitrogen atmosphere, 124 mg (0.216 mmol) of palladium bis (benzylideneacetone) and 130 mg (0.648 mmol) of tri-tert-butylphosphine were dissolved in 20 ml of xylene and stirred at room temperature for 15 minutes. Thereto was added 1 g (1.08 mmol) of a tetrabromo (9,9-dimethylfluorene) dibromo dissolved in 50 ml of xylene, and the mixture was stirred for 30 minutes on an oil bath heated to 50 ° C. Further, 694 mg (2.59 mmol) of N- (1-anthracenyl) -N- (phenyl) amine was dissolved in 20 ml of xylene and added dropwise, followed by 374 mg (3.89 mmol) of sodium tert-butoxide. The mixture was heated and stirred for about 7 hours on an oil bath heated to 130 ° C. After returning the reaction solution to room temperature, 50 ml of water was added, the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene and ethyl acetate, combined with the previous organic layer, and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene: hexane = 1: 2). 900 mg of 71b was obtained.
[0091]
<Example 3>
An organic light emitting device having the structure shown in FIG. 3 was prepared by the following method.
[0092]
What formed indium tin oxide (ITO) as an anode 2 with a film thickness of 120 nm on a glass substrate as a substrate 1 by a sputtering method was used as a transparent conductive support substrate. This was ultrasonically washed successively with acetone and isopropyl alcohol (IPA), then boiled and washed with IPA and then dried. Furthermore, what was UV / ozone cleaned was used as a transparent conductive support substrate.
[0093]
Using a compound represented by the following structural formula as a hole transport material, a chloroform solution was prepared so that the concentration was 0.5 wt%.
[0094]
Embedded image
This solution was dropped on the anode 2, and a film was formed by spin coating first at a rotation of 500 RPM for 10 seconds and then at a rotation of 1000 RPM for 1 minute. Thereafter, the film was dried in a vacuum oven at 80 ° C. for 10 minutes to completely remove the solvent in the thin film. The thickness of the formed hole transport layer was 50 nm.
[0096]
Next, as the light emitting layer 3 on the hole transport layer 5, the exemplified compound Nos. 2a was vapor-deposited and the 20 nm light emitting layer 3 was provided. The degree of vacuum at the time of vapor deposition was 1.0 × 10 −4 Pa, and the film formation rate was 0.2 to 0.3 nm / sec.
[0097]
Furthermore, aluminum quinolinol (Alq3) was formed as the electron transport layer 6 to a film thickness of 40 nm by vacuum deposition. The degree of vacuum at the time of deposition was 1.0 × 10 −4 Pa and the film formation rate was 0.2 to 0.3 nm / sec.
[0098]
Next, using a vapor deposition material made of an aluminum-lithium alloy (lithium concentration 1 atom%), a metal layer film having a thickness of 10 nm is formed on the organic layer by a vacuum vapor deposition method. An organic light-emitting device having an aluminum film having a thickness of 150 nm and an aluminum-lithium alloy film as an electron injection electrode (cathode 4) was prepared. The degree of vacuum at the time of vapor deposition was 1.0 × 10 −4 Pa, and the film formation rate was 1.0 to 1.2 nm / sec.
[0099]
The obtained organic EL device was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive so that the device did not deteriorate due to moisture adsorption.
[0100]
In the device thus obtained, with an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode, an emission luminance of 1600 cd / m 2 and a maximum luminance of 9100 cd / m at an applied voltage of 6V. 2. Luminescence with a luminous efficiency of 1.25 lm / W was observed.
[0101]
<Examples 4 to 9>
Exemplified Compound No. A device was prepared in the same manner as in Example 3 except that the compounds shown in Table 1 were used in place of 2a, and the same evaluation was performed. The results are shown in Table 1.
[0102]
[Table 1]
<Example 10>
An organic light emitting device having the structure shown in FIG. 3 was prepared by the following method.
[0104]
In the same manner as in Example 3, a hole transport layer 5 was formed on a transparent conductive support substrate.
[0105]
Next, as the light emitting layer 3 on the hole transport layer 5, the exemplified compound Nos. 6b was vapor-deposited and the 20 nm light emitting layer 3 was provided. The degree of vacuum at the time of vapor deposition was 1.0 × 10 −4 Pa, and the film formation rate was 0.2 to 0.3 nm / sec.
[0106]
Furthermore, bathophenanthroline (BPhen) was formed into a film with a thickness of 40 nm by a vacuum evaporation method, and the electron transport layer 6 was formed. The degree of vacuum at the time of vapor deposition was 1.0 × 10 −4 Pa, and the film formation rate was 0.2 to 0.3 nm / sec.
[0107]
Next, the cathode 4 was formed in the same manner as in Example 1 and then sealed.
[0108]
The device thus obtained has a light emission luminance of 2250 cd / m 2 and a maximum luminance of 11750 cd / m at an applied voltage of 6 V, with the ITO electrode (anode 2) as the positive electrode and the Al—Li electrode (cathode 4) as the negative electrode. 2. Luminescence with a luminous efficiency of 1.39 lm / W was observed.
[0109]
<Examples 11 to 14>
Exemplified Compound No. A device was prepared in the same manner as in Example 10 except that the compounds shown in Table 2 were used in place of 6b, and the same evaluation was performed. The results are shown in Table 2.
[0110]
[Table 2]
<Example 15>
As the light emitting layer 3, the exemplified compound No. 1 is used. 23 and the exemplified compound Nos. A device was prepared in the same manner as in Example 3 except that 120 (weight ratio 4: 100) was co-evaporated and the 20 nm light-emitting layer 3 was provided.
[0112]
The device thus obtained has a light emission luminance of 1100 cd / m 2 , a maximum luminance of 27700 cd / m 2 and a light emission efficiency of 2 at an applied voltage of 4 V, with the ITO electrode 2 as the positive electrode and the Al—Li electrode 4 as the negative electrode. An emission of 25 lm / W was observed.
[0113]
<Examples 16 to 18>
Exemplified Compound No. A device was prepared in the same manner as in Example 15 except that the compounds shown in Table 3 were used in place of 23, and the same evaluation was performed. The results are shown in Table 3.
[0114]
[Table 3]
<Examples 19 to 21>
Exemplified Compound No. A device was prepared in the same manner as in Example 15 except that the compounds shown in Table 4 were used in place of 120, and the same evaluation was performed. The results are shown in Table 4.
[0116]
[Table 4]
<Example 22>
As the light emitting layer 3, the exemplified compound No. 1 is used. 23 and the exemplified compound Nos. A device was prepared in the same manner as in Example 10 except that 120 (weight ratio 4: 100) was co-evaporated and the 20 nm light-emitting layer 3 was provided.
[0118]
The device thus obtained was subjected to a light emission luminance of 1890 cd / m2, a maximum luminance of 29200 cd / m2, a light emission efficiency of 2.50 lm / m2 with an applied voltage of 4 V using the ITO electrode 2 as the positive electrode and the Al-Li electrode 4 as the negative electrode. W emission was observed.
[0119]
<Examples 23 to 25>
Exemplified Compound No. A device was prepared in the same manner as in Example 15 except that the compounds shown in Table 5 were used in place of 23, and the same evaluation was performed. The results are shown in Table 5.
[0120]
[Table 5]
<Examples 26 to 28>
Exemplified Compound No. A device was prepared in the same manner as in Example 15 except that the compounds shown in Table 6 were used in place of 120, and the same evaluation was performed. The results are shown in Table 6.
[0122]
[Table 6]
<Example 29>
The device produced in Example 26, where a voltage was applied for 100 hours with the current density kept to 7.0 mA / cm 2 in a nitrogen atmosphere, 100 hours after the initial luminance 400cd / m 2, 380cd / m 2 and the luminance degradation Was small.
[0124]
<Examples 30 to 34>
The emission spectra of the devices prepared in Examples 4, 5, 11, 19, and 22 were observed with MCPD-7000, and CIE chromaticity coordinates were measured. The results are shown in Table 7.
[0125]
[Table 7]
<Comparative Example 1>
A device was prepared in the same manner as in Example 10 except that the following comparative compound was used as the light emitting layer 3.
[0127]
Embedded image
The device thus obtained, the ITO electrode 2 positive electrode and the Al-Li electrode 4 in the anode, at an applied voltage of 6V, light emission luminance 940 cd / m 2, the maximum brightness 5050cd / m 2, luminous efficiency 0. A light emission of 63 lm / W was observed.
[0129]
Further, the emission spectrum of this device was observed with MCPD-7000 and the CIE chromaticity coordinates were measured, and it was (x, y) = (0.16, 0.29).
[0130]
<Comparative example 2>
A device was fabricated in the same manner as in Example 10 except that the comparative compound and the exemplified compound 129 (weight ratio 4: 100) were co-evaporated as the light emitting layer 3 to provide the 20 nm light emitting layer 3.
[0131]
The device thus obtained has an emission luminance of 1060 cd / m 2 , a maximum luminance of 9270 cd / m 2 , a luminous efficiency of 0. A light emission of 82 lm / W was observed.
[0132]
Moreover, when the emission spectrum of this element was observed with MCPD-7000 and the CIE chromaticity coordinates were measured, it was (x, y) = (0.16, 0.27).
[0133]
【The invention's effect】
As described above, the organic light-emitting device using the compound represented by the general formula [1] exhibits a light emission hue with extremely high purity, and has a light output with high efficiency, high luminance, and long life. In particular, an organic layer containing a compound represented by the general formula [1] is excellent as a light emitting layer.
[0134]
Furthermore, the element can also be formed by using vacuum deposition or a casting method, and an element having a relatively low cost and a large area can be easily formed.
[Brief description of the drawings]
FIG. 1 is a cross-sectional view showing an example of an organic light emitting device in the present invention.
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device according to the present invention.
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device according to the present invention.
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
FIG. 5 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
[Explanation of symbols]
DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Light emitting layer 4 Cathode 5 Hole transport layer 6 Electron transport layer 7 Hole injection layer 8 Hole / exciton blocking layer
Claims (3)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003006796A JP3848262B2 (en) | 2002-03-27 | 2003-01-15 | Oligofluorenylene compound and organic light-emitting device |
| PCT/JP2003/003615 WO2003080559A1 (en) | 2002-03-27 | 2003-03-25 | Oligofluorenylene compounds |
| KR1020047014970A KR100644913B1 (en) | 2002-03-27 | 2003-03-25 | Oligofluorenylene compounds |
| EP03712917A EP1487779A1 (en) | 2002-03-27 | 2003-03-25 | Oligofluorenylene compounds |
| AU2003221098A AU2003221098A1 (en) | 2002-03-27 | 2003-03-25 | Oligofluorenylene compounds |
| CNB038012987A CN1291969C (en) | 2002-03-27 | 2003-03-25 | Oligofluorenylene compounds |
| US10/506,300 US7229702B2 (en) | 2002-03-27 | 2003-03-25 | Oligofluorenlylene compounds |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002088918 | 2002-03-27 | ||
| JP2003006796A JP3848262B2 (en) | 2002-03-27 | 2003-01-15 | Oligofluorenylene compound and organic light-emitting device |
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| Publication Number | Publication Date |
|---|---|
| JP2004002298A JP2004002298A (en) | 2004-01-08 |
| JP2004002298A5 JP2004002298A5 (en) | 2005-05-26 |
| JP3848262B2 true JP3848262B2 (en) | 2006-11-22 |
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| JP2003006796A Expired - Fee Related JP3848262B2 (en) | 2002-03-27 | 2003-01-15 | Oligofluorenylene compound and organic light-emitting device |
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| Country | Link |
|---|---|
| US (1) | US7229702B2 (en) |
| EP (1) | EP1487779A1 (en) |
| JP (1) | JP3848262B2 (en) |
| KR (1) | KR100644913B1 (en) |
| CN (1) | CN1291969C (en) |
| AU (1) | AU2003221098A1 (en) |
| WO (1) | WO2003080559A1 (en) |
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| JP4311707B2 (en) * | 2002-08-28 | 2009-08-12 | キヤノン株式会社 | Organic light emitting device |
| JP4164317B2 (en) * | 2002-08-28 | 2008-10-15 | キヤノン株式会社 | Organic light emitting device |
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| JP4065547B2 (en) * | 2004-04-12 | 2008-03-26 | キヤノン株式会社 | Fluorene compound and organic light emitting device using the same |
| WO2005123634A1 (en) | 2004-06-16 | 2005-12-29 | Idemitsu Kosan Co., Ltd. | Fluorene derivative and organic electroluminescent device using same |
| JP4086817B2 (en) | 2004-07-20 | 2008-05-14 | キヤノン株式会社 | Organic EL device |
| JP2006140235A (en) * | 2004-11-10 | 2006-06-01 | Idemitsu Kosan Co Ltd | Organic electroluminescence element |
| JP4599142B2 (en) * | 2004-11-26 | 2010-12-15 | キヤノン株式会社 | Organic light emitting device |
| JP4429149B2 (en) * | 2004-11-26 | 2010-03-10 | キヤノン株式会社 | Fluorene compound and organic light emitting device |
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| WO2006060435A2 (en) * | 2004-12-03 | 2006-06-08 | Sumitomo Chemical Company, Limited | Triarylamine containing polymers and electronic devices |
| JPWO2006062078A1 (en) * | 2004-12-08 | 2008-06-12 | 出光興産株式会社 | Organic electroluminescence device |
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| JP5164389B2 (en) * | 2006-03-28 | 2013-03-21 | キヤノン株式会社 | Amino compound for organic light emitting device and organic light emitting device having the same |
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| GB2440934B (en) | 2006-04-28 | 2009-12-16 | Cdt Oxford Ltd | Opto-electrical polymers and devices |
| JP4865411B2 (en) * | 2006-06-15 | 2012-02-01 | キヤノン株式会社 | Organic light emitting device, display device and display device |
| CN100439470C (en) * | 2006-11-07 | 2008-12-03 | 南京大学 | Polymer material displaying blue light and preparation method thereof |
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| JP4827771B2 (en) * | 2007-03-08 | 2011-11-30 | キヤノン株式会社 | Organic light emitting device and display device using oligofluorene compound |
| JP5127300B2 (en) * | 2007-05-28 | 2013-01-23 | キヤノン株式会社 | Fluorene compound, organic light emitting device using the same, and display device |
| JP5196928B2 (en) * | 2007-09-18 | 2013-05-15 | キヤノン株式会社 | Organic light emitting device and display device |
| JP5202017B2 (en) * | 2008-02-14 | 2013-06-05 | ケミプロ化成株式会社 | Bis (tetrafluorenyl) amine compound, method for producing the same, light emitting material using the same, hole transport material, and organic EL device |
| JP5732463B2 (en) * | 2009-10-05 | 2015-06-10 | トルン ライティング リミテッドＴｈｏｒｎ Ｌｉｇｈｔｉｎｇ Ｌｉｍｉｔｅｄ | Multi-layer organic element |
| JP5691192B2 (en) * | 2010-02-24 | 2015-04-01 | 東洋インキＳｃホールディングス株式会社 | Material for organic electroluminescence device and use thereof |
| JP6444046B2 (en) | 2013-04-03 | 2018-12-26 | キヤノン株式会社 | Organic compound and organic light emitting device |
| TWI838352B (en) * | 2017-11-24 | 2024-04-11 | 德商麥克專利有限公司 | Materials for organic electroluminescent devices |
| CN109929095A (en) * | 2018-12-31 | 2019-06-25 | 华南理工大学 | A kind of blue light conjugated polymer luminescent material and the preparation method and application thereof based on double sulphur oxindoles carbazole units |
| CN109929094A (en) * | 2018-12-31 | 2019-06-25 | 华南理工大学 | A kind of blue light frequency-doubling luminescent material and the preparation method and application thereof based on anthra sulphur dibenzofuran unit |
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| DE69110922T2 (en) | 1990-02-23 | 1995-12-07 | Sumitomo Chemical Co | Organic electroluminescent device. |
| JP2998187B2 (en) | 1990-10-04 | 2000-01-11 | 住友化学工業株式会社 | Organic electroluminescence device |
| US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
| JPH05202356A (en) | 1991-09-11 | 1993-08-10 | Pioneer Electron Corp | Organic electroluminescence element |
| JP3328731B2 (en) | 1991-12-05 | 2002-09-30 | 住友化学工業株式会社 | Organic electroluminescence device |
| DE69608446T3 (en) * | 1995-07-28 | 2010-03-11 | Sumitomo Chemical Company, Ltd. | 2.7 ARYL 9 SUBSTITUTED FLUORESE AND 9 SUBSTITUTED FLUORESOLIGOMERS AND POLYMERS |
| JPH09202878A (en) | 1996-01-25 | 1997-08-05 | Nippon Telegr & Teleph Corp <Ntt> | Near ultraviolet or ultraviolet region light-emission element |
| JPH09227576A (en) | 1996-02-23 | 1997-09-02 | Sony Corp | Metallic multinuclear complex, its production and optical element |
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| EP0879868B1 (en) | 1997-05-19 | 2002-04-03 | Canon Kabushiki Kaisha | Organic compound and electroluminescent device using the same |
| US6387544B1 (en) * | 1998-04-10 | 2002-05-14 | The Trustees Of Princeton University | OLEDS containing thermally stable glassy organic hole transporting materials |
| JP2001052868A (en) | 1999-08-05 | 2001-02-23 | Idemitsu Kosan Co Ltd | Organic electroluminescent element |
| KR20050084516A (en) | 1998-12-28 | 2005-08-26 | 이데미쓰 고산 가부시키가이샤 | Organic electroluminescent element |
| US6100405A (en) * | 1999-06-15 | 2000-08-08 | The United States Of America As Represented By The Secretary Of The Air Force | Benzothiazole-containing two-photon chromophores exhibiting strong frequency upconversion |
| JP4220624B2 (en) | 1999-07-30 | 2009-02-04 | 三井化学株式会社 | Amine compounds |
| EP1149827B1 (en) * | 2000-04-26 | 2003-12-10 | Sony International (Europe) GmbH | End-capped polyfluorenes, films and devices based thereon |
| US20010051487A1 (en) | 2000-04-26 | 2001-12-13 | Yuichi Hashimoto | Method for making organic luminescent device |
| WO2003020847A1 (en) * | 2001-09-03 | 2003-03-13 | Canon Kabushiki Kaisha | Organic luminescence device |
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- 2003-01-15 JP JP2003006796A patent/JP3848262B2/en not_active Expired - Fee Related
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| CN1291969C (en) | 2006-12-27 |
| US7229702B2 (en) | 2007-06-12 |
| KR100644913B1 (en) | 2006-11-14 |
| AU2003221098A1 (en) | 2003-10-08 |
| CN1568303A (en) | 2005-01-19 |
| KR20040095308A (en) | 2004-11-12 |
| EP1487779A1 (en) | 2004-12-22 |
| JP2004002298A (en) | 2004-01-08 |
| US20050106414A1 (en) | 2005-05-19 |
| WO2003080559A1 (en) | 2003-10-02 |
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